Compound SF-1 is disclosed and claimed in the PCT application, published as WO 2008/115,369, as a potent inhibitor of Focal Adhesion Kinase (FAK). Example 10 of the published PCT application provides the structure and a synthesis of compound SF-1, termed compound 6 therein.

The preparation of SF-1 was carried out in two steps from available precursor materials. In a first step 2-chloro-4-iodo-5-trifluoromethylpyridine was condensed with the N-methyl amide of anthranilic acid to provide intermediate SF-Int2A.

In the second step, SF-Int2A was condensed with o-methoxy-p-N-morpholinoaniline (SM3) to yield SF-1 in free base form.

The free base form of SF-1 was subsequently converted to a hydrochloride salt and purified by recrystallization from dioxane.
Both couplings used the Pd2(dba)3/xantphos system as catalyst. Pd2(dba)3 is tris(dibenzylideneacetone)dipalladium(0). Xantphos is 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene.
The efficacy of this exemplary compound as an inhibitor of Focal Adhesion Kinase (FAK) has made scaleable, high-yield synthetic routes desirable for large scale production of the compound and closely analogous compounds that may also prove to be effective inhibitors of FAK.